I want Calibre to send newly downloaded feeds to my Kindle using e-mail. That way, I don't have to connect Kindle and the PC using a cable.

There is an automated E-mail feature, but it only seems to allow SMTP with TSL/SSL server. The problem is, this is a cooperate environment and the port to GMail is blocked. I can only send e-mails using Outlook. How can I do that? Is there any plug-in for that?

PS:
I tried to search this forum for "Outlook" but the almost 500 results seemed to be irrelevant. I opened a few but they didn't even contain the work "Outlook". I guess the search system is wrong.

There is no built-in support for Outlook. Calibre is cross-platform and Outlook is Windows specific so I expect there is no great interest in developing such an interface. Kovid as the main developer is Linux based and does not run Windows.